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Jane Pratt, Unbound and Ready for the Web

THE model Veronica Webb made charming faces at the camera. Michael Stipe, the lead vocalist for R.E.M., cozied up to a snake. The actor David Arquette designed a T-shirt that read: “I love. Therefore I am.”

Friends of the former magazine editor Jane Pratt, they and other members of the Pratt Pack — the rapper Estelle; the designer Isaac Mizrahi; and the models Carol Alt, Helena Christensen and Crystal Renn — showed up last month for a series of photo shoots at Drive-In Studios to help promote xoJane.com, Ms. Pratt’s new Web site, which went live on Monday.

The name of the site, which was originally and rather unimaginatively called JanePratt.com, “has a personal feel to it and is in keeping with the spirit and the content of the site,” Ms. Pratt said. The name change occurred little more than a week before the site’s twice-delayed debut (originally May 2, then May 12).

With verticals on fashion; beauty; sports; entertainment; DIY; technology; New Agey; and Sex, Sex, Sex and Love, xoJane.com is the latest chapter in the Jane Pratt story, a saga that began almost 25 years ago with the debut of Sassy, a magazine for teenagers. Then 24, she was put in charge, introducing a postmodern writing style that Time called “pajama-party journalism.” Articles like “Losing Your Virginity” and “Why Your Breasts Aren’t as Weird as You Think” were sprinkled liberally with of-the-moment slang — “daggy” — and bracketed asides and commentary from Ms. Pratt, who, it quickly became clear, had her finger on adolescents’ fluttery pulse.

Jane, aimed at Sassy graduates, followed in 1997 with regular features like Jane’s Diary and Jane Needs Help, articles like “Do You Have a Disease or Are You Just in Your 20s” and an attention-getting story on young women selling their eggs. Ms. Pratt left the magazine in 2005; it folded in 2007.

Along the way, there have been two short-lived TV talk shows. And for the last four years, Ms. Pratt, the single mother of an 8-year-old daughter, Charlotte, has had a weekly call-in show, “Jane Radio,” on SiriusXM. On satellite radio, as in the pages of Sassy and Jane, she has both dispensed advice and sought it, ostentatiously laying out her maternal malfeasance on the segment Worst Mom in the World. She let Charlotte stay up past her bedtime! She let Charlotte wear the same clothes to school two days in a row! Celebrity cronies like Courtney Cox and Mr. Stipe sometimes drop by the studio to chat.

Ms. Pratt, who is 48 but looks younger (she credits this to occasional brief binges of zinc tablets), has perfected the art of likability and of making her regard seem like an honor. But some feel that her cast of characters has grown a bit old hat. This may help explain the collaboration with the 15-year-old Style Rookie blogger Tavi Gevinson on a related site for teenage girls, tentatively called Wallflower and set to make its debut this fall.

For now, Ms. Pratt is engaged in what is the struggle for celebrity editors (see: Brown, Tina): how to reinvent or reconfigure her personal brand for the digital age.

“When I left Jane I wanted to do something in the Internet arena,” she said. “I felt like: ‘Where are my readers now? Where are those people I want to reach?’ They’re online, same as I am. I’m not at newsstands buying up copies of print magazines.”

Photo

Jane Pratt is attempting to reconfigure her personal brand for the digital age.Credit
Lee Clower for The New York Times

Still, she said, both of her new sites may have occasional print editions.

If Sassy was the anti-Seventeen and Jane the anti-Glamour, xoJane.com, aimed at women age 18 to 49, is the anti-iVillage. “It’s more risk-taking and, of course, edgier,” Ms. Pratt said. “It’s not hard to be edgier than iVillage.”

Rubrics on the site like Do the Don’t (wear white while you have your period, for example, or try a tanning bed), Jane Needs Help and Makeunders (celebrities and civilians get de-glammed) will be recognizable to Sassy and Jane readers. So will the site’s tone, which will be personal, familiar and chatty. Freelancers and staff members like the beauty editor Cat Marnell, a Lucky alumna; the tech editor Natalie Podrazik and a contributor, Elna Baker, are promoted on the site as Cat, Natalie and Elna.

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When writers post their articles, “I’m going to be in there making comments as to whether I agree with them,” said Ms. Pratt who, via Inside Jane’s Phone, will be inviting interested parties to browse through her photos and text messages. Friends like Tatum O’Neal, Ms. Cox, Courtney Love and Patti Smith will be contributors to the site, she said, adding: “I’ve gone back and forth with Mariah Carey about doing something. I had her on the cover of Jane, and we always liked each other. She’s a girl’s girl. That’s the bottom line for me.”

Any product that is mentioned will be available for purchase on the site or through links to others. “If I’m recommending cashew water and I think it’s better than coconut water, you can buy that,” Ms. Pratt said. Some items, like the shirt Mr. Arquette wore during his photo shoot, will be made expressly for sale on the site. Advertisers include Ford, General Motors, L’Oréal and Unilever, said Troy Young, the president of SAY Media, the company that is backing the site.

“I think it’s really smart of her to go to the Web; her lens is unique,” said Mary Berner, the former chief executive of Fairchild, the publisher of Jane. “So many of the women-focused sites out there are undifferentiated and boring. If anyone can nail a voice that’s distinct, it’s Jane. I think she’s absolutely brilliant.”

Indeed, Ms. Pratt is arguably the Helen Gurley Brown of her era: an insider who finds it useful to pose as an outsider, who has a particular I-thou connection with readers and whose every obsession and concern show up in a story. (Though Ms. Brown had more mainstream success as the longtime editor of Cosmopolitan.)

At a recent xoJane.com editorial meeting, snacks like fruit and Starburst candy seemed to precisely reflect the site’s ethos: healthy and sensible or fun and utterly without nutritional value. Ms. Pratt, in a ponytail and small-lens glasses, discussed a feature of the site that will send couples on a blind date and have them make a Twitter post about it in real time, then checked the progress of a Do the Don’t.

“Are you going to do ‘crying at work?’ ” she asked Liz Armstrong, who will write about lesbian relationships for the site and act as New Age editor.

“I did it by accident,” Ms. Armstrong said. “I looked at my ex’s Facebook page yesterday, and it really bummed me out, and I cried in front of my assistant.”

The tears-at-the-office idea seemed young for a large part of the site’s intended demographic, as did a suggestion for an I’ll Try Anything Once feature: walking around for the day in a nude unitard or going to a makeup counter and asking to be given a fake black eye. But perhaps it’s not so easy for Ms. Pratt to abandon the age group that has served her so well.

“It’s really gratifying when someone comes up to me and I can tell they’re going to say, ‘I was a Sassy reader,’ or ‘I was a Jane reader,’ ” she said. “I can tell because of a certain confidence they have. I see that these women are doing amazing things in their lives. It makes me feel proud, and it makes me feel old.”

A version of this article appears in print on May 19, 2011, on Page E8 of the New York edition with the headline: Jane Pratt, Unbound and Ready for the Web. Order Reprints|Today's Paper|Subscribe